Sodium Iodide → 7-[2-(4-Hydroxy-piperidin-1-yl)-ethoxy]-4-(-indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 1595805Notes

Reaction equation

HRID 1595805 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([CH:22]=[N:23][NH:24]4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28].[OH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[I-].[Na+]>COCCOC>[OH:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([NH:17][C:18]4[CH:26]=[C:25]5[C:21]([CH:22]=[N:23][NH:24]5)=[CH:20][CH:19]=4)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]3)=[CH:7][C:6]=2[O:27][CH3:28])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 79341Piperidin-4-olHCID 102940037-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 101615617-[2-(4-Hydroxy-piperidin-1-yl)-ethoxy]-4-(-indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
135 °C

Procedure

Using an analogous procedure to that described in Example 157, 196.5 mg (0.5 mmol) of the 7-(2-chloro-ethoxy)-4-(1H-indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile, 505.8 mg (5.0 mmol) of 4-hydroxypiperidine and 75.0 mg (0.5 mmol) of sodium iodide in 5 mL of DME was heated at 135° C. for 16 hr. The work up gave 97.9 mg (42.8%) of the product as a off white solid, m.p. 174° C. (dec.), mass (electrospray, m/e): M+H 459.0.

Sources & evidence

ORD record
ord-d9dada9550d148e89b6e405060d4c624
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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